Triethylamine → HCID 57385996, compound

HRID 2406855Notes

Reaction equation

HRID 2406855 reaction equation
[CH2:1]([OH:8])[C@@H:2]([OH:7])[CH2:3][CH2:4][C:5]#[CH:6].C(N([CH2:14][CH3:15])CC)C.[C:16]1(C)[C:17]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:19]=C[CH:21]=1>C(Cl)Cl.C([Sn](=O)CCCC)CCC>[OH:7][C@@H:2]([CH2:3][CH2:4][C:5]#[CH:6])[CH2:1][O:8][S:22]([C:17]1[CH:18]=[CH:19][C:14]([CH3:15])=[CH:21][CH:16]=1)(=[O:24])=[O:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 24808701HCID 24808701, compound

Product 1

HCID 57385996HCID 57385996, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 61221Dibutyltin oxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Diol (1) (1.560 g, 13.667 mmol) was dissolved in DCM (140 mL) cooled to 0° C. and dibutyltin oxide (67.9 mg, 0.2728 mmol), triethylamine (2.08 mL, 1.518 g, 15.005 mmol) and toluenesulfonyl chloride (2.864 g, 15.022 mmol) were added. After 10 minutes the icebath was removed and the reaction mixture was stirred for 22 hours. Then it was filtrated and the filtrate concentrated in vacuo. Purification by chromatography (hexane/EtOAc 4/1) provided 2.950 g of compound (2a) as clear colourless oil with 80% yield.

Workup

  1. customAfter 10 minutes the icebath was removed
  2. filtrationThen it was filtrated
  3. concentrationthe filtrate concentrated in vacuo
  4. customPurification by chromatography (hexane/EtOAc 4/1)

Sources & evidence

ORD record
ord-85d91a524c6a472f81469e2938a7134c
Source dataset
uspto-grants-2014_08
Patent number
US08809395B2

Reaction notes

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